CA2080223C - Thiophene sulfonamides useful as carbonic anhydrase inhibitors - Google Patents

Thiophene sulfonamides useful as carbonic anhydrase inhibitors Download PDF

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Publication number
CA2080223C
CA2080223C CA002080223A CA2080223A CA2080223C CA 2080223 C CA2080223 C CA 2080223C CA 002080223 A CA002080223 A CA 002080223A CA 2080223 A CA2080223 A CA 2080223A CA 2080223 C CA2080223 C CA 2080223C
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CA
Canada
Prior art keywords
alkoxy
substituted
alkyl
halogen
nr5r6
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
CA002080223A
Other languages
English (en)
French (fr)
Other versions
CA2080223A1 (en
Inventor
Thomas Robert Dean
Hwang-Hsing Chen
Jesse Albert May
Anura Pathmaciri Dantanarayana
Daniel Kuzmich
Paul W. Zinke
Raymond Eugene Conrow
Michael E. Deason
Mark Thomas Dupriest
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Alcon Vision LLC
Original Assignee
Alcon Laboratories Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Alcon Laboratories Inc filed Critical Alcon Laboratories Inc
Publication of CA2080223A1 publication Critical patent/CA2080223A1/en
Application granted granted Critical
Publication of CA2080223C publication Critical patent/CA2080223C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
CA002080223A 1990-04-09 1991-04-03 Thiophene sulfonamides useful as carbonic anhydrase inhibitors Expired - Lifetime CA2080223C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US50673090A 1990-04-09 1990-04-09
US506,730 1990-04-09
US618,765 1990-11-27
US07/618,765 US5153192A (en) 1990-04-09 1990-11-27 Thiophene sulfonamides useful as carbonic anhydrase inhibitors
PCT/US1991/002262 WO1991015486A1 (en) 1990-04-09 1991-04-03 Thiophene sulfonamides useful as carbonic anydrase inhibitors

Publications (2)

Publication Number Publication Date
CA2080223A1 CA2080223A1 (en) 1991-10-10
CA2080223C true CA2080223C (en) 2000-11-07

Family

ID=27055558

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002080223A Expired - Lifetime CA2080223C (en) 1990-04-09 1991-04-03 Thiophene sulfonamides useful as carbonic anhydrase inhibitors

Country Status (20)

Country Link
US (2) US5153192A (pt)
EP (1) EP0527801B1 (pt)
JP (1) JP2562394B2 (pt)
KR (1) KR100196414B1 (pt)
AT (1) ATE221527T1 (pt)
AU (1) AU655924B2 (pt)
BR (1) BR9106330A (pt)
CA (1) CA2080223C (pt)
DE (3) DE10299054I1 (pt)
DK (1) DK0527801T3 (pt)
ES (1) ES2180530T3 (pt)
FI (2) FI924553A0 (pt)
HK (1) HK1014186A1 (pt)
IL (1) IL97800A (pt)
LU (2) LU90935I2 (pt)
NL (2) NL300098I2 (pt)
NO (1) NO923948L (pt)
NZ (1) NZ237754A (pt)
WO (1) WO1991015486A1 (pt)
ZA (1) ZA912580B (pt)

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US5344929A (en) * 1993-02-18 1994-09-06 Alcon Laboratories, Inc. Preparation of carbonic anhydrase inhibitors
US5538966A (en) * 1994-01-21 1996-07-23 Alcon Laboratories, Inc. Carbonic anhydrase inhibitors
AU1684895A (en) * 1994-01-21 1995-08-08 Alcon Laboratories, Inc. Thienothiazine sulfonamide derivatives process and intermediates for their preparation and their use as carbonic anhydrase inhibitors
US5646142A (en) * 1994-07-08 1997-07-08 Alcon Laboratories, Inc. Thiophene sulfonamides useful as carbonic anhydrase inhibitors
US6316443B1 (en) 1994-08-04 2001-11-13 Merck & Co., Inc. Ophthalmic compositions comprising combinations of a carbonic anhydrase inhibitor and a β-adrenergic antagonist
US5464831A (en) * 1994-09-09 1995-11-07 Alcon Laboratories, Inc. Thienothiadiazine sulfonamides useful as carbonic anhydrase inhibitors
US5510347A (en) * 1994-09-09 1996-04-23 Alcon Laboratories, Inc. Thienothiadiazine sulfonamides useful as carbonic anhydrase inhibitors
US5470973A (en) * 1994-10-03 1995-11-28 Alcon Laboratories, Inc. Synthesis of sulfonamide intermediates
US5620970A (en) * 1995-06-05 1997-04-15 Alcon Laboratories, Inc. Topical ophthalmic carbonic anhydrase inhibitor formulations
US6172054B1 (en) 1995-06-15 2001-01-09 Alcon Laboratories, Inc. Combination therapy for lowering and controlling intraocular pressure
WO1997002825A1 (en) * 1995-07-12 1997-01-30 Alcon Laboratories, Inc. Thiophene sulfonamides useful as carbonic anhydrase inhibitors
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US6441047B2 (en) 1995-11-17 2002-08-27 Alcon Manufacturing Ltd.. Combination therapy for treating glaucoma
TR199801665T2 (xx) * 1996-02-26 1998-12-21 Advanced Research & Technology Institute Makular �demin engellenmesi i�in karbonik anhidraz inhibit�rlerinin kullan�m�.
US5900427A (en) * 1996-05-03 1999-05-04 Wisconsin Alumni Research Foundation N-heteroarenesulfonyl-protected amino acid reagents for peptide synthesis
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BR9814497A (pt) 1997-12-23 2000-10-10 Alcon Lab Inc Processo para prevenir ou retardar perda de campo visual associada com glaucoma ou hipertensão ocular
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US6960579B1 (en) * 1998-05-19 2005-11-01 Alcon Manufacturing, Ltd. Serotonergic 5HT7 receptor compounds for treating ocular and CNS disorders
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JP5881514B2 (ja) * 2012-04-09 2016-03-09 株式会社トクヤマ アミン誘導体の製造方法
JP5914246B2 (ja) * 2012-08-10 2016-05-11 株式会社トクヤマ ブリンゾラミドの精製方法
CN102936236A (zh) * 2012-11-13 2013-02-20 江苏吉贝尔药业有限公司 一种布林佐胺中间体(3-乙酰基-5-氯-2-(苄基巯基)噻酚)的制备方法
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UA116273C2 (uk) 2013-10-17 2018-02-26 Сентісс Фарма Прайвет Лімітед Офтальмологічний фармацевтичний склад, що не містить консерванта
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UA118576C2 (uk) 2014-01-24 2019-02-11 Сентис Фарма Прайвет Лімітед Фармацевтична композиція, яка містить бринзоламід
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JP2020504711A (ja) 2016-12-21 2020-02-13 バイオセリックス， インコーポレイテッド タンパク質を標的とすることにおいて使用するための、チエノピロール誘導体、その組成物、方法、および使用
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DE1096916B (de) * 1957-12-17 1961-01-12 Hoechst Ag Verfahren zur Herstellung von Thiophen-3, 5-disulfonamiden
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Also Published As

Publication number Publication date
IL97800A (en) 1997-08-14
NZ237754A (en) 1992-08-26
KR930700490A (ko) 1993-03-15
HK1014186A1 (en) 1999-09-24
US5153192A (en) 1992-10-06
LU91555I2 (fr) 2009-06-22
ZA912580B (en) 1992-01-29
IL97800A0 (en) 1992-06-21
DE69133080T2 (de) 2003-03-27
EP0527801B1 (en) 2002-07-31
CA2080223A1 (en) 1991-10-10
DK0527801T3 (da) 2002-11-25
NL300098I1 (nl) 2002-11-01
FI924553A (fi) 1992-10-08
JPH05508832A (ja) 1993-12-09
US5240923A (en) 1993-08-31
EP0527801A4 (en) 1993-03-10
AU655924B2 (en) 1995-01-19
NO923948D0 (no) 1992-10-09
DE122009000026I1 (de) 2010-01-28
WO1991015486A1 (en) 1991-10-17
EP0527801A1 (en) 1993-02-24
ES2180530T3 (es) 2003-02-16
NO923948L (no) 1992-12-08
BR9106330A (pt) 1993-04-20
ATE221527T1 (de) 2002-08-15
FI963424A0 (fi) 1996-09-02
FI963424A (fi) 1996-09-02
NL300098I2 (nl) 2003-01-06
FI924553A0 (fi) 1992-10-08
DE10299054I1 (de) 2006-06-08
DE69133080D1 (de) 2002-09-05
NL300389I1 (nl) 2009-07-01
LU90935I2 (en) 2002-09-05
JP2562394B2 (ja) 1996-12-11
KR100196414B1 (ko) 1999-06-15
AU7746791A (en) 1991-10-30

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